Synthesis of 4-methoxyphenylacetonitrile

Preparation of 4-methoxyphenylacetonitrile

In a 2-litre two-necked flask fitted with a reflux condenser (protected with calcium chloride tube) and mechanical stirrer, 1 mole of  the 1-(chloromethyl)-4-methoxybenzene (or any other halide), 1.5 mole of finely powdered sodium cyanide dried at 105°C, 0.05 mole of sodium iodide, and 500 ml of DRY acetone are boiled under reflux for 20 hours. Then the reaction mixture is cooled to room temperature and is filtered from sodium chloride with suction, and the salt is washed with 200 ml of acetone. The acetone is distilled off from the combined filtrates, and the residue is fractionated in vacuo at 94°C/0.4 mmHg, yielding 80% of 4-methoxyphenylacetonitrile.

Organicum. Practical Handbook of Organic Chemistry, by Heinz Becker, Werner Berger and Günter Domschke, Addison-Wesley Pub. Co, 223-226, (1973)

IUPAC Name

2-(4-methoxyphenyl)acetonitrile

InChI

InChI=1S/C9H9NO/c1-11-9-4-2-8(3-5-9)6-7-10/h2-5H,6H2,1H3

InChI Key

PACGLQCRGWFBJH-UHFFFAOYSA-N

Canonical SMILES

COC1=CC=C(C=C1)CC#N

Depositor-Supplied Synonyms

4-Methoxyphenylacetonitrile, 104-47-2, 4-Methoxybenzyl cyanide, 2-(4-methoxyphenyl)acetonitrile, (4-methoxyphenyl)acetonitrile, p-Methoxyphenylacetonitrile, p-Methoxybenzyl cyanide, 4-Anisyl cyanide, Benzeneacetonitrile, 4-methoxy-, Anisylacetonitrile, p-Methoxybenzeneacetonitrile, Acetonitrile, (p-methoxyphenyl)-, NSC 96, 4-Methoxybenzylcyanide, ANISYL CYANIDE, 4-METHOXYBENZENEACETONITRILE, 4-methoxyphenyl acetonitrile, (p-methoxyphenyl)acetonitrile, (4-Methoxyphenyl) acetonitrile, (4-Methoxy-phenyl)-acetonitrile, 2-(4-methoxyphenyl)ethanenitrile, PACGLQCRGWFBJH-UHFFFAOYSA-N, EINECS 203-206-0, MFCD00001919, SBB055070, BRN 0509162, NSC96, p-Anisyl cyanide, p-Anisylacetonitrile, p-methoxybenzylcyanide, HOMOANISONITRILE, PubChem20331, 4-(Cyanomethyl)anisole, 4-methoxy benzyl cyanide, 4-methoxy-benzyl cyanide, AC1Q4CDQ, 4-methoxyphenylacetnitrile, p-Methoxy phenylacetonitrile, p-methoxyphenyl acetonitrile, 4-methoxy phenylacetonitrile, AC1L24GW, KSC492S5N, SCHEMBL103029, (4-methoxy-phenyl)acetonitrile, ACMC-2098c4, 169986_ALDRICH, NSC-96, PARAGOS 510025, CHEMBL2228958, CTK3J2956, PACGLQCRGWFBJH-UHFFFAOYSA-, 2-(4-methoxyphenyl)-acetonitrile, MolPort-001-759-770, OTAVA-BB 1779154, 4-Methoxyphenylacetic acid nitrile, HMS1748O04, ZINC157051, ACT07150, STR00862, ANW-15074, LABOTEST-BB LT00848055, LABOTEST-BB LT03331265, STL164355, ZINC00157051, AKOS000198026, AC-2495, AS01654, CS13459, MCULE-5855306851, RP17347, RTC-030997, TRA0003891, AJ-14858, AK-46718, AN-13936, BR-46718, CJ-01580, KB-39581, LS-13281, OR034011, OR146939, TS-03569, ZB006532, KB-193145, ST2411514, TC-030997, AM20020127, FT-0618955, M0856, ST50824094, AZ0001-0335, M-6278, 4-10-00-00555 (Beilstein Handbook Reference), A800985, 3B4-0170, Q-200492, S01-0596, T5449391, InChI=1/C9H9NO/c1-11-9-4-2-8(3-5-9)6-7-10/h2-5H,6H2,1H3

Removed Synonyms

4-Methoxyphenol, 3-Methoxyphenylacetonitrile, C9H9NO, CID66031

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